Carbon-Fluorine Activation in the Gas Phase: The Reactions of Benzyl C-F Bonds and Silyl Cations.

The activation of C-F bonds figures largely in both fundamental and applied chemical processes. Herein the activation of benzyl C-F bonds by silyl cations is examined both computationally and experimentally in the gas phase. The experimental rate constant values obtained herein have not heretofore been measured and provide insight into the intrinsic ability of silyl cations to activate C-F bonds. Trends in reactivity and correlations between theoretical and experimental data are discussed in the context of C-F bond cleavage.